M-Anilide-urethanes

ABSTRACT

New m-anilide-urethanes, processes for their manufacture, herbicides containing these compounds, and processes for controlling unwanted plant growth with these compounds.

This is a continuation of application Ser. No. 086,134, filed Oct. 18,1979 now abandoned.

The present invention relates to new m-anilide-urethanes, processes fortheir manufacture, herbicides containing these compounds, and processesfor controlling unwanted plant growth with these compounds.

It has been disclosed (German Pat. No. 1,542,836) that important,commercially available herbicides such as3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide are, in spite oftheir excellent action on many weed species, ineffective against anumber of important unwanted plants. By contrast, m-anilidoureas, e.g.,2,4-dichlorophenoxyacetic acid-(3'-(N'-methylureido)-anilide, do have asomewhat broader spectrum of action, combating broadleaved and grassyweeds, but the literature gives no indication of a pronounced toleranceby crop plants, which would enable them to be used as selectiveherbicidal agents (German Printed Application DE-AS No. 1,793,226).

U.S. Pat. No. 3,979,202 discloses numerous 3'-(carbamoyloxy)-anilides,e.g., 3'-N-isopropylcarbamoyloxypropionanilide, which have widelyvarying herbicidal actions on higher plants-they may be used asherbicides or as agents for reducing the height of crop plants, and atrates of from 0.1 to 10 lbs of active ingredient per acre.

We have now found that m-anilide-urethanes of the formula ##STR1## whereA, B and D are identical or different and each denotes oxygen or sulfur,R¹ denotes unsubstituted alkyl; alkyl substituted by halogen, alkoxy,alkoxycarbonyl or cyano; unsubstituted or halogen-substituted alkenyl;unsubstituted or halogen- or alkoxy-substituted alkynyl; or R¹ denotesunsubstituted or alkyl-substituted cycloalkyl or aryl, R² and R³ areidentical or different and each denotes hydrogen, alkyl, alkoxyalkyl orhaloalkyl, R⁴ denotes alkylene of 1 to 6 carbon atoms which isunsubstituted or substituted by alkyl, alkoxyalkyl or haloalkyl, Xdenotes hydrogen, alkyl, haloalkyl, alkoxy, halogen, nitro or amino, Ydenotes hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, aralkyl,halogen, an alkenyl chain fused with the benzene ring to give asubstituted or unsubstituted naphthyl ring, Y further denotes alkoxy,haloalkoxy, alkylthio, nitro, aryl, thiocyanato, cyano, ##STR2## R⁵ andR⁶ being identical or different and each denoting hydrogen or having themeanings given for R¹, m denotes one of the integers 1, 2, 3 and 4, andn denotes one of the integers 1, 2, 3, 4 and 5, have a good herbicidalaction on numerous important unwanted plants. They are tolerated byvarious crop plants without, or with only very minor, damage.

The radicals in the general formula may for instance have the followingmeanings:

R¹ : unsubstituted alkyl, or alkyl substituted by halogen, alkoxy,alkoxycarbonyl or cyano (e.g., methyl, ethyl, 2-chloroethyl,2-methoxyethyl, methoxycarbonylmethyl, isopropyl, n-propyl, n-butyl,sec-butyl, tert-butyl, isobutyl, cyanomethyl), unsubstituted orhalogen-substituted alkenyl (e.g., allyl, 2-chloropropen-(1)-yl-(3),buten-(1)-yl-(3)), unsubstituted or halogen- or alkoxy-substitutedalkynyl (e.g., propargyl, butyn-(1)-yl-(3), 1-chlorobutyn-(2)-yl-(4)),unsubstituted or alkyl-substituted cycloalkyl (e.g., cyclopentyl,cyclohexyl, 3-methylcyclohexyl, 2,6-dimethylcyclohexyl, cycloheptyl,4-tert-butylcyclohexyl), or aryl (e.g., phenyl);

R² and R³, independently of each other: hydrogen, alkyl (e.g., methyl,ethyl, isopropyl), alkoxyalkyl (e.g., methoxymethyl, 2-methoxyethyl), orhaloalkyl (e.g., chloromethyl, 2-chloroethyl);

R⁴ : alkylene of 1 to 6 carbon atoms which is unsubstituted orsubstituted by alkyl, alkoxyalkyl or haloalkyl (e.g., methylene,methylmethylene, dimethylmethylene, propylene, hexylene,chloromethylmethylene, methoxymethylmethylene, ethylmethylene,methylethylene, isopropylmethylene, 1-chloromethylethylene,methoxyethylmethylene, 2-chloroethylmethylene, diethylmethylene,ethylene, methylpropylene, butylene, dimethylethylene, propylmethylene);

X: hydrogen, alkyl (e.g., methyl), haloalkyl (e.g., trifluoromethyl),alkoxy (e.g., methoxy), halogen (e.g., fluorine, chlorine, bromine andiodine), nitro or amino;

Y: hydrogen, alkyl (e.g., methyl, isopropyl), haloalkyl (e.g.,trifluoromethyl), alkoxyalkyl (e.g., methoxymethyl), cycloalkyl (e.g.,cyclohexyl), aralkyl (e.g., benzyl), halogen (e.g., fluorine, chlorine,bromine and iodine), an alkenyl chain which is fused with the benzenering to give a substituted or unsubstituted naphthyl ring, alkoxy (e.g.,methoxy), haloalkoxy (e.g., trifluoromethoxy), alkylthio (e.g.,methylthio), nitro, aryl (e.g., phenyl), thiocyanato, cyano, ##STR3## R⁵and R⁶ being identical or different and each denoting hydrogen or havingthe meanings given for R¹.

The new compounds may be prepared for instance by the following methods,A, B, D, R¹, R², R³, R⁴, X, Y, m and n having the above meanings. Theterms "urethanes" and "chloroformates" as used hereinafter shall alsocover thiono-, thio- and dithiourethanes, and chloroformic acidthionoesters, chloroformic acid thioesters and chloroformic aciddithioesters. ##STR4##

It will be clear from the foregoing diagrams how interrelated thestarting materials are. It will also be apparent that, depending on thenature of the substituents A, B, D, R¹, R², R³, R⁴, X and Y and on theavailability of the reactants, one route may be more advantageous thananother.

Starting from prior art m-nitranilines (A), m-nitrophenyliso(thio)-cyanates (B) may be prepared (W. Siefken, J. Liebigs Annalender Chemie, 562, 75 et seq., 1949), which in turn smoothly react withthe components R¹ -AH to give the nitro(thio)urethanes (C) (S. Petersen,Methoden der Organ. Chemie, VIII, 131 Georg-Thieme-Verlag, Stuttgart,4th ed., 1952), which, however, are also directly accessible fromm-nitranilines (A) with chloroformates (R¹ A-CB-Cl) (German Laid-OpenApplication DE-OS No. 1,643,763) or with carbon disulfide or carbonoxysulfide, base and alkylating agent (Methoden der Organ. Chemie, IX,831 et seq., Georg-Thieme-Verlag, Stuttgart, 4th ed., 1955). Reductionthen gives the aminourethanes (D, R³ =H), (S. Schroter, Methoden derOrgan. Chemie, XI/1, 350 et seq., Georg-Thieme-Verlag, Stuttgart, 4thed., 1957), which are acylated, either direct or after conversion to theproduct monosubstituted on the amino nitrogen (D, R³ ≠H) (Methoden derOrgan. Chemie, XI/1, 24 et seq., Georg-Thieme-Verlag, Stuttgart, 4thed., 1957), with phenoxycarboxylic acids, phenoxycarboxylic acidhalides, esters or anhydrides to give the m-anilide-urethanes accordingto the invention (Methoden der Organ. Chemie, XI/2, 3 et seq.,Georg-Thieme-Verlag, Stuttgart, 4th ed., 1958).

The aminourethanes (D) may also first be reacted with a halocarboxylicacid, halocarboxylic acid halide, ester or anhydride to give them-anilide-urethanes (E), which then react with phenols or thiophenols togive the m-anilide-urethanes according to the invention (Methoden derOrgan. Chemie, VI/3, 54 et seq., Georg-Thieme-Verlag, Stuttgart, 4thed., 1965).

A further synthesis route is to react m-nitroanilines (A) withphenoxycarboxylic acids, phenoxycarboxylic acid halides, esters oranhydrides to give m-nitroanilides (G), which are also accessible vianitrohalides (F).

Reduction of the m-nitroanilides (G) gives the m-aminoanlides (H, R²=H), which may be reacted, either directly or after conversion to theproduct monosubstituted on the amino nitrogen (H, R² ≠H), withchloroformates (R¹ ACB-Cl) or with carbon disulfide or carbonoxysulfide, base and alkylating agent to give the m-anilide-urethanesaccording to the invention.

The preferred synthesis steps are described in more detail below.

(a) The reaction of 3-nitrophenyl iso(thio)cyanates (B) is carried outwith or without a catalyst usually used for iso(thio)cyanate reactions,e.g., tertiary amines (triethylamine, 1,4-diazabicyclo-(2,2,2)-octane),nitrogenous heterocyclic compounds (pyridine, 1,2-dimethylimidazole) ororganic tin compounds (dibutyltin diacetate, dimethyltin dichloride), ifdesired in a solvent inert under the reaction conditions, e.g.,hydrocarbons (ligroin gasoline, toluene, pentane, cyclohexane),halohydrocarbons (methylene chloride, chloroform, dichloroethane,chlorobenzene, o-, m- and p-dichlorobenzene), nitrohydrocarbons(nitrobenzene, nitromethane), nitriles (acetonitrile, butyronitrile,benzonitrile), ethers (diethyl ether, tetrahydrofuran, dioxane), esters(ethyl acetate, methyl propionate), ketones (acetone, methyl ethylketone), or amides (dimethylformamide, formamide)(German Laid-OpenApplication DE-OS No. 1,568,138), at from 0° to 150° C., preferably 40°to 100° C.

(b) 3-nitranilines (A) and 3-aminoanilides (H) are reacted withchloroformates in a suitable solvent, e.g., water, alcohols (methanol,ethanol, isopropanol), or as under (a), with the aid of a conventionalacid binder, e.g., alkali metal hydroxides, carbonates and bicarbonates,alkaline earth metal oxides, hydroxides, carbonates and bicarbonates, ortertiary organic bases (e.g., triethylamine, pyridine,N,N-dimethylamine, N,N-dimethylcyclohexylamine, quinoline ortributylamine), or starting material 3-nitraniline, at from -20° to+150° C., preferably from +20° to 80° C.

(c) The nitrourethanes (C) and nitroanilides may be reduced by one ofthe conventional processes, e.g., by catalytic hydrogenation, with ametal/acid combination, e.g., a combination of iron and acid, or with ametal/alcohol combination, e.g., zinc dust and aqueous alcohol, or ironand aqueous alcohol.

(d) 3-Nitroanilines (A) and aminourethanes (D) are reacted withphenoxycarboxylic acid halides or with halocarboxylic acid halides in asuitable solvent, with the addition of a conventional acid binder asgiven under (a), at from -20° to +150° C., preferably from 0° to 60° C.

Instead of the acid halides, the acids themselves may also be used ifthey are activated with an aliphatic carbodiimide, e.g.,dicyclohexylcarbodiimide. Particularly suitable solvents of those givenunder (a) e.g., tetrahydrofuran; the preferred temperature range is from0° to 60° C.

The 3-nitranilines (A) and aminourethanes (D) are reacted withphenoxycarboxylic acid esters either without a solvent or in anindifferent solvent, such as hydrocarbons (toluene), halohydrocarbons(dichlorobenzene) or amides (dimethylformamide), at from 50° to 180° C.,preferably from 80° to 150° C.

(e) The haloamide urethanes (E) and the nitrohaloamides (F) are reactedeither with alkali metal (thio)phenolates in an indifferent solvent asunder (a), or with finely pulverized potassium carbonate and(thio)phenol in a ketone (acetone, methyl ethyl ketone), at from 0° to150° C., preferably from 40° to 100° C.

The following examples illustrate the preparation of the newm-anilide-urethanes and their precursors.

I. Nitrourethanes EXAMPLE A

87 Parts by weight of sodium bicarbonate is added to 138 parts by weightof m-nitraniline in 500 parts by weight of tetrahydrofuran. Whilestirring, 120 parts by weight of thiomethyl chloroformate is dripped inat room temperature, the mixture is stirred for 16 hours at roomtemperature and then filtered, the solvent is distilled off in a rotaryevaporator, and the oil which is obtained is stirred into toluene. Thecrystals which separate out are filtered and dried; m.p.: 137°-138° C.

The compound has the following structural formula: ##STR5##

EXAMPLE B

51 Parts by weight of tert-butanol is added to 112 parts by weight of3-nitrophenyl isocyanate in 600 parts by weight of toluene. A few dropsof triethylamine are added after 4 hours, and the mixture is allowed tostand for 48 hours. White crystals are obtained after removal of thesolvent in vacuo. Melting point: 97°-99° C.

The compound has the following structural formula: ##STR6##

The following nitrourethanes (C) may be prepared analogously:

    ______________________________________                                         ##STR7##                                                                     A   B     X       R.sup.1          R.sup.2                                                                            m.p. °C.                       ______________________________________                                        O   O     H       CH.sub.3         H    153-155                               O   S     H       CH.sub.3         H                                          O   O     6-CH.sub.3                                                                            CH.sub.3         H    132-133                               O   O     H       phenyl           H    123-125                               O   O     H       phenyl           CH.sub.3                                                                           69-70                                 O   O     6-F     phenyl           H    138-140                               O   O     5-CF    CH.sub.3         H    86-87                                 O   O     6-CH.sub.3                                                                            C.sub.2 H.sub.5  H    131-133                               O   O     H       C.sub.2 H.sub.5  H    64-66                                 O   O     2-CH.sub.3                                                                            phenyl           H    112-114                               O   O     4-CH.sub.3                                                                            CH.sub.3         H    114-117                               O   O     H       cyclooctyl       H    103-105                               O   O     H       CH.sub.2 COOCH.sub.3                                                                           H    123-125                               O   O     5-CF.sub.3                                                                            CH(CH.sub.3).sub.2                                                                             H    121-123                               O   O     H       CH.sub.3         CH.sub.3                                                                           58-61                                 O   O     H       3,5-dimethylcyclohexyl                                                                         H    128-129                               O   O     H       CH(CH.sub.3).sub.2                                                                             H    86-88                                 O   O     6F      CH.sub.3         H    116-118                               O   O     4Cl     phenyl           H    125-127                               O   O     4Cl     CH.sub.3         H    122-124                               O   O     4-CH.sub.3                                                                            C.sub.2 H.sub.5  H    80-81                                 O   O     H       1-methylcyclopentyl                                                                            H    57-59                                 O   O     5-CF.sub.3                                                                            phenyl           H    133-135                               O   O     H       2,6-dimethylcyclohexyl                                                                         H    121-123                               O   O     6OCH.sub.3                                                                            CH.sub.3         H    134-136                               O   O     H       cycloheptyl      H    102-104                               O   O     6OCH.sub.3                                                                            phenyl           H    209-211                               O   S     H       phenyl           H                                          O   O     H       cyclopentyl      H    110-112                               O   O     6Cl     CH.sub.3         H    136-138                               O   O     H       3-methylcyclohexyl                                                                             H    120-122                               S   S     H       CH.sub.3         H                                          S   O     H       C(CH.sub.3).sub.3                                                                              H                                          S   O     H       C.sub.2 H.sub.5  H                                          S   O     H       phenyl           H    156-158                               O   O     C.sub.2 H.sub.5                                                                       phenyl           H    56-58                                 O   O     H       C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                              H    62-63                                 O   O     H       CH(CH.sub.2 OCH.sub.3).sub.2                                                                   H    95-96                                 O   O     H       cyclohexyl       H    117-118                               ______________________________________                                    

II. Aminourethanes EXAMPLE C

While stirring vigorously, 40 parts by weight of3-(S-methylthiocarbamoyl)-nitrobenzene is added to a mixture, heated at80° C., of 33 parts by weight of iron powder, 75 parts by weight ofalcohol, 60 parts by weight of water and 3 parts by weight ofconcentrated hydrochloric acid in such portions that the temperature iskept at 80° C. without additional heating. The mixture is then refluxedfor 1 hour and filtered hot, the residue and the filtrate are digestedwith about 1,000 parts by weight of methylene chloride, followed bydrying over sodium sulfate, concentration and recrystallization fromtoluene; m.p.: 101°-103° C.

Structure: ##STR8##

The following aminourethanes (D) may be prepared analogously:

    ______________________________________                                         ##STR9##                                                                     A   B     X       R.sup.1         R.sup.2                                                                            m.p. °C.                        ______________________________________                                        O   O     H       CH.sub.3        H    87-89                                  O   O     6CH.sub.3                                                                             CH.sub.3        H                                           O   O     H       phenyl          CH.sub.3                                                                           70-72                                  O   O     4F      CH.sub.3        H                                           O   S     H       CH.sub.3        H                                           S   O     H       C.sub.2 H.sub.5 H                                           O   S     H       phenyl          H                                           O   O     5CF.sub.3                                                                             CH.sub.3        H    viscous oil                            O   O     H       C.sub.2 H.sub.5 H    viscous oil                            O   O     2CH.sub.3                                                                             phenyl          H    131-133                                O   O     4CH.sub.3                                                                             CH.sub.3        H                                           O   O     4Cl     phenyl          H    215-217                                O   O     4Cl     CH.sub.3        H                                           O   O     4CH.sub.3                                                                             C.sub.2 H.sub.5 H                                           S   S     H       phenyl          H                                           O   O     H       3,3,5-trimethylcyclohexyl                                                                     H    100-102                                O   O     H       phenyl          C.sub.2 H.sub.5                                                                    104-106                                O   O     H       cyclopentyl     H                                           O   O     5-CF.sub.3                                                                            phenyl          H    214-216                                O   O     H       phenyl          H    178-180                                O   O     H       1-methylcyclopentyl                                                                           H                                           O   O     H       hexahydrobenzyl H    106-108                                O   O     6OCH.sub.3                                                                            CH.sub.3        H    85-87                                  O   O     H       cycloheptyl     H    86-88                                  O   O     6OCH.sub.3                                                                            phenyl          H    84-86                                  O   O     6Cl     CH.sub.3        H                                           O   O     H       3-methylcyclohexyl                                                                            H    95-97                                  O   O     H       CH.sub.2 COOCH.sub.3                                                                          H    viscous oil                            S   S     H       CH.sub.3        H                                           O   O     H       C(CH.sub.3).sub.3                                                                             H    109-110                                O   O     5-CF.sub.3                                                                            CH(CH.sub.3).sub.2                                                                            H    102-104                                O   O     H       CH.sub.3        CH.sub.3                                                                           89-92                                  O   O     H       3,5-dimethylcyclohexyl                                                                        H    80-82                                  O   O     H       CH(CH.sub.3).sub.2                                                                            H    66-68                                  O   O     4F      CH.sub.3        H                                           O   O     H       C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                             H    65-67                                  O   O     H       cyclohexyl      H    122-124                                ______________________________________                                    

III. Nitrohaloamides and haloamide urethanes EXAMPLE D

126 parts by weight of sodium bicarbonate is added to 138 parts byweight of 3-nitroaniline in 1,500 parts by weight of ethyl acetate. At0° to 10° C. and while stirring, 216 parts by weight of 2-bromopropionylbromide is dripped in, the mixture is then stirred for 16 hours at roomtemperature, filtered and concentrated, and the crystals which areobtained are washed with toluene; m.p.: 99°-101° C.

The compound has the following structural formula (cf. F): ##STR10##

The following haloamide urethanes (E) may be prepared analogously:

    __________________________________________________________________________     ##STR11##                                                                    A B  X   R.sup.2                                                                           R.sup.1                                                                           R.sup.3                                                                          R.sup.4   Hal m.p. °C.                             __________________________________________________________________________    O O  H   H   methyl                                                                            H  CH(CH.sub.3)                                                                            Cl  138-141                                     O O  H   H   methyl                                                                            H  CH.sub.2  Cl  168-170                                     S S  H   H   methyl                                                                            H  CH(CH.sub.3)                                                                            Cl                                              O O  H   H   methyl                                                                            H  C(CH.sub.3).sub.2CH.sub.2                                                               Cl  125-127                                     O O  H   H   methyl                                                                            H  CH(C.sub.2 H.sub.5)                                                                     Br  131-133                                     O O  H   H   ethyl                                                                             H  CH.sub.2  Cl                                              O O  H   H   methyl                                                                            H  C(CH.sub.3).sub.2                                                                       Br  91-93                                       O O  4CH.sub.3                                                                         H   methyl                                                                            H  CH(CH.sub.3)                                                                            Br  207-210                                     O O  H   H   methyl                                                                            H  (CH.sub.2).sub.3                                                                        Cl                                              S O  H   H   methyl                                                                            H  CH(CH.sub.3)                                                                            Br  160-162                                     O O  H   H   methyl                                                                            H  CH(CH.sub.3)                                                                            Br  142-143                                     O S  H   H   methyl                                                                            H  CH(CH.sub.3)                                                                            Br                                              O O  H   H   phenyl                                                                            H  CH.sub.2  Cl  170-173                                     O O  H   CH.sub.3                                                                          methyl                                                                            H  CH(CH.sub.3)                                                                            Cl                                              O O  H   H   phenyl                                                                            H  C(CH.sub.3).sub.2CH.sub.2                                                               Cl  143-145                                     O O  H   H   phenyl                                                                            H  CH(CH.sub.3)                                                                            Cl  170-172                                     O O  H   H   methyl                                                                            CH.sub.3                                                                         CH(CH.sub.3)                                                                            Br                                              __________________________________________________________________________

IV. 3-Nitro- and 3-aminoanilides EXAMPLE E

At room temperature and while stirring well, 254 parts by weight ofα-(2,4-dichlorophenoxy)-propionyl chloride is dripped into a mixture of152 parts of N-methyl-3-nitroaniline, 126 parts by weight of sodiumbicarbonate and 800 parts by weight of ethyl acetate. The mixture isstirred for 16 hours at room temperature and then filtered, the solventis distilled off in a rotary evaporator, and the residue is stirred withpetroleum ether, filtered and dried; m.p.: 125°-127° C.

The compound has the following structural formula: ##STR12##

EXAMPLE F

62 parts by weight of 3-nitroaniline and 96.5 parts by weight ofα-(2-methyl-4-chlorophenoxy)-propionic acid are dissolved in 300 partsby weight of tetrahydrofuran. While stirring and at room temperature,102 parts by weight of dicyclohexylcarbodiimide in 200 parts by weightof tetrahydrofuran is slowly added. After the mixture has been stirredfor 16 hours it is filtered and concentrated, and the residue isdissolved in ethyl acetate, shaken with 5% strength sodium hydroxidesolution, 5% strength hydrochloric acid and water, dried andconcentrated. The residue is recrystallized from methanol. Meltingpoint: 124°-127° C.

The compound has the following structural formula: ##STR13##

EXAMPLE G

A mixture of 219 parts by weight of α-(2,4-dichlorophenoxy)-propionicacid-m-nitroanilide, 7 parts by weight of 10% palladium on animalcharcoal and 2,000 parts by weight of tetrahydrofuran is hydrogenated atroom temperature and atmospheric pressure. After the theoreticalhydrogen absorption, the mixture is filtered, freed from solvent andcrystallized with petroleum ether. Melting point: 125°-128° C.

The compound has the following structural formula: ##STR14##

The following 3-nitroanilides (G) and 3-aminoanilides (H) may beprepared analogously:

    ______________________________________                                         ##STR15##                                                                    Z    X       R.sup.3                                                                              R.sup.4   D     Y     m.p. °C.                     ______________________________________                                        NO.sub.2                                                                           H       H      CH(CH.sub.3)                                                                            O   2,4-Cl.sub.2                                                                          164-166                             NO.sub.2                                                                           H       H      CH.sub.2  O   2,4-Cl.sub.2                                                                          203-205                             NO.sub.2                                                                           4F      H      CH(CH.sub.3)                                                                            O   2CH.sub.3 4Cl                               NO.sub.2                                                                           H       CH.sub.3                                                                             CH(CH.sub.3)                                                                            O   2,4,5Cl.sub.3                               NO.sub.2                                                                           H       H      (CH.sub.2).sub.3                                                                        O   2,4Cl.sub.2                                 NO.sub.2                                                                           H       H      CH(CH.sub.3)                                                                            S   H                                           NO.sub.2                                                                           H       H      CH(CH.sub.3)                                                                            O   2,4(CH.sub.3).sub.2                         NO.sub.2                                                                           H       H      CH(CH.sub.3)                                                                            O   3Cl                                         NO.sub.2                                                                           6OCH.sub.3                                                                            H      CH(CH.sub.3)                                                                            O   2,4-Cl.sub.2                                                                          185-187                             NH.sub.2                                                                           H       H      CH(CH.sub.3)                                                                            O   2,4Cl.sub.2                                                                           131-134                             NH.sub.2                                                                           H       H      CH(CH.sub.3)                                                                            O   2CH.sub.34Cl                                                                          82-84                               NH.sub.2                                                                           H       H      CH.sub.2  O   2,4Cl.sub.2                                                                           125-127                             NH.sub.2                                                                           4F      H      CH(CH.sub.3)                                                                            O   2CH.sub.34Cl                                NH.sub.2                                                                           H       CH.sub.3                                                                             CH(CH.sub.3)                                                                            O   2,4,5Cl.sub.3                               NH.sub.2                                                                           H H     CH(CH.sub.2).sub.3)                                                                  O         2,4Cl.sub.2                                     NH.sub.2                                                                           H       H      CH(CH.sub.3)                                                                            S   H                                           NH.sub.2                                                                           H       H      CH(CH.sub.3)                                                                            O   2,4(CH.sub.3)                               NH.sub.2                                                                           H       H      CH(CH.sub.3)                                                                            O   3Cl                                         ______________________________________                                    

V. m-Anilide-urethanes EXAMPLE 1

21.1 Parts by weight of methyl α-(3-chlorophenoxy)-propionate and 16.3parts by weight of 3-(O-methoxycarbamoyl)-aniline are kept at 130° C.for 48 hours. The crude product is chromatographed on silica gel using amixture of 95 parts of methylene chloride and 5 parts of methanol. Whitecrystals are obtained which melt at 129°-131° C. and have the followingstructural formula: ##STR16##

EXAMPLE 2

At room temperature, 3.8 parts by weight of thiomethyl chloroformate isdripped into a mixture of 10.5 parts by weight ofα-(2-methyl-4-chlorophenoxy)-propionic acid-(m-aminoanilide), 6 parts byweight of sodium bicarbonate and 150 parts by weight of tetrahydrofuran.After the mixture has been stirred for 10 hours, it is filtered andconcentrated. The oil which is obtained is crystallized withtoluene/petroleum ether. Melting point: 148°-150° C.

The compound has the following structural formula: ##STR17##

EXAMPLE 3

At room temperature and while stirring well, 24.8 parts by weight ofα-(2,4-dichlorophenoxy)-propionyl chloride is dripped into a mixture of11.6 parts by weight of 3-(O-methylcarbamoxyl)-aniline, 10.5 parts byweight of sodium bicarbonate and 200 parts by weight of tetrahydrofuran.The mixture is stirred for 16 hours at room temperature and thenfiltered, the solvent is distilled off in a rotary evaporator and theresidue is recrystallized from diethyl ether. Melting point: 108°-110°C.

The compound has the following structural formula: ##STR18##

EXAMPLE 4

157 Parts by weight of 3-(O-methylcarbamoyl)-aniline and 200 parts byweight of α-(2-methyl-4-chlorophenoxy)-propionic acid are dissolved in600 parts by weight of tetrahydrofuran. While stirring and at roomtemperature, 191 parts by weight of dicyclohexylcarbodiimide in 500parts by weight of tetrahydrofuran is slowly added. After 3 hours themixture is filtered and concentrated, and the residue is dissolved inethyl acetate, shaken with 5% strength (by weight) sodium hydroxidesolution, 5% strength hydrochloric acid and water, dried andconcentrated. The residue is recrystallized from methanol. Meltingpoint: 114°-115° C.

The compound has the following structural formula: ##STR19##

EXAMPLE 5

25.7 Parts by weight of α-chloropropionicacid-3-(O-methylcarbamoyl)-anilide, 22.7 g of sodium-4-chlorophenolateand 200 parts by weight of acetonitrile are boiled for 14 hours. Afterfiltration and concentration, the residue is taken up in methylenechloride and shaken with dilute sodium hydroxide solution. After dryingover sodium sulfate, the solvent is distilled off and the residue ischromatographed on silica gel using methylene chloride. White crystalsare obtained which melt at from 148° to 151° C. The compound has thefollowing structural formula: ##STR20##

The following compounds may be prepared analogously:

      ##STR21##      NO. A B D R.sup.1 R.sup.2 R.sup.3 R.sup.4 X Y m.p. °C.      6 O O O C.sub.2 H.sub.5 H H CH(CH.sub.3) H 2,4Cl.sub.2 83-85 7 O O O     CH.sub.3 CH.sub.3 H CH(CH.sub.3) H 2,4Cl.sub.2 120-122 8 O O O CH.sub.3     H CH.sub.3 CH(CH.sub.3) H 2,4Cl.sub.2 161-163 9 S O O t-C.sub.4 H.sub.9     H H CH(CH.sub.3) H 2,4Cl.sub.2 119-121 10 O S S CH.sub.2 CH.sub.2     OCH.sub.3 C.sub.2      H.sub.5 H (CH.sub.2).sub.2 5-CH.sub.3 4N(CH.sub.3).sub. 2 11 O S O     C.sub.2 H.sub.5 H CH.sub.2 OCH.sub.3 C(C.sub.2 H.sub.5)(CH.sub.2     Cl)CH.sub.2 H 4-SCH.sub.3 12 O O O CH.sub.2 CN H H CH(CH.sub.3) H     2,4Cl.sub.2 84-85 13 S O O CH.sub.3 iC.sub.3 H.sub.7 H CH(CH.sub.3) H     3SO.sub.2 CH.sub.3 14 O O S CH.sub.3 H H CH(iC.sub.3 H.sub.7) H 4Cl     142-144 15 S S O CH.sub.3 H H CH(CH.sub.3) H 2,4Cl.sub.2 137-139 16 O O     O CH.sub.3 CH.sub.2 OCH.sub.3 H CH(CH.sub.3) H 4OCF.sub.2 CHF.sub.2 17 O     O O CH.sub.3 H H CH.sub.2 H 2,4,5Cl.sub.3 179-181 18 O O O CH.sub.3 H     C.sub.2 H.sub.5 CH(CH.sub.3) H 3CH.sub.2 OCH.sub.3 19 O O O i-C.sub.3     H.sub.7 H H CH(CH.sub.3) H 2,4Cl.sub.2 152-154 20 S O O C.sub.2 H.sub.5     CH.sub.2 CH.sub.2 OCH.sub.3 H  CH(CH.sub.3) H 4 cyclohexyl 21 S S S     CH.sub.3 3 H CH(CH.sub.3) H 3-NHCOCH.sub.3 22 O O O CH.sub.2 CCH H H     CH(CH.sub.3) H 2,4Cl.sub.2 111-113 23 O O O CH.sub.3 H i-C.sub.3 H.sub.7 C     H.sub.2 H 2,4 J.sub.2 24 O O O CH.sub.3 CH.sub.2      Cl CH.sub.3 CH(CH.sub.3) H 2,4Cl.sub.2 25 O O O CH.sub.3 H H CH(C.sub.2     H.sub.5) H 2,4Cl.sub.2 101-103 26 O O O CH.sub.3 H H CH(CH.sub.2     OCH.sub.3) H 2Br 4Cl 124-126 27 O S S CH.sub.3 H H CH(CH.sub.3 ) H     2,4Cl.sub.2 28 O O O CH.sub.2 CH.sub.2 OCH.sub.3 H H CH(CH.sub.3) H     2,4Cl.sub.2 viscous oil 29 O O O CH.sub.3 H H C(CH.sub.3).sub.2 H     2,4Cl.sub.2 147-148 30 O O O CH.sub.3 H H CH(CH.sub.2 Cl) H 2CH.sub.3     4Cl 31 S O S CH.sub.3 H H CH(CH.sub.3) H 2,4Cl.sub.2 32 O O O CH.sub.2     CH.sub.2 Cl H H CH(CH.sub.3) H 2,4Cl.sub.2 59-61 33 S S S C.sub.2     H.sub.5 CH.sub.3 H CH(CH.sub.2 CH.sub.2 OCH.sub.3)CH.sub.2 4CH.sub.3 3     SCN 34 O O O CH.sub.3 H H C(CH.sub.3)(C.sub.2 H.sub.5) H 2CH.sub.3 4Cl     35 O O O CH.sub.2 COOCH.sub.3 H H CH(CH.sub.3) H 2,4Cl.sub.2 146-148 36     O O O CH.sub.3 H H (CH.sub.2).sub.3 H 2,4Cl.sub.2 110-112 37 O S O     CH.sub.2 CCH H CH.sub.3 CH(CH.sub.2 CH.sub.2 Cl) 6Cl 3-COOCH.sub.3 38 O     O O CH.sub.2 CHCH.sub.2 H H CH(CH.sub.3) H 2,4Cl.sub.2 76-78 39 O O O     CH.sub.3 H H C(C.sub.2 H.sub.5).sub.2 H 2Br 4Cl 40 O O O CH.sub.3 H H     CH.sub.2 H 2,4Cl.sub.2 189-190 41 O O O t-C.sub.4      H.sub.9 H H CH(CH.sub.3) H 2,4Cl.sub.2 88-89 42 O O O CH.sub.3 H H     C(CH.sub.3)(CH.sub.2 Cl) H 2CH.sub.3      4Cl 43 S O O CH.sub.3 H H (CH.sub.2).sub.2 H 2,4,5Cl.sub.3 44 S O O     CH.sub.2 CH.sub.2 CN H H CH(CH.sub.3) H 2F 4Br 45 O O O cycl. C.sub.7     H.sub.13 H H CH(CH.sub.3) H 2,4Cl.sub.2 82-84 46 O O O CH.sub.3 H H     CH(CH.sub.3) 6-Cl 2,4Cl.sub.2 47 S O O CH.sub.3 H CH.sub.3 CH(CH.sub.3)     H 2,4Cl.sub.2 188-190      48 O O O     ##STR22##      C.sub.2 H.sub.5 H CH(CH.sub.3) H 2,4Cl.sub.2 97-98      49 O O O CH(CH.sub.3)CH.sub.2      CN H H CH(CH.sub.3) H 3-NHCON(CH.sub.3).sub.2 50 O O O CH.sub.3 H H     CH(CH.sub.3) H 2Cl 4Br 122-124 51 O O O CH.sub.3 H H CH.sub.2 H H     155-156 52 O O O CH.sub.3 H H CH(CH.sub.3) H 2Br 4Cl 145-147 53 O O O     CH.sub.3 H H CH(CH.sub.3) H 4F 110-111 54 O O O CH(CH.sub.3)CN H H     CH(nC.sub.3 H.sub.7) H 3 CONHCH.sub.3 55 O O O C.sub.2 H.sub.5 H     CH.sub.3 CH(CH.sub.3) H 2,4Cl.sub.2 150-153 56 O O O i-C.sub.4 H.sub.9 H     H CH(CH.sub.3) H 2Br 4Cl 57 O O O CH.sub.3 H H CH(CH.sub.3) H 2Cl     138-140 58 O O O CH.sub.3 H H CH(CH.sub.3) H 4Br 153-155 59 O O O     CH.sub.2CClCH.sub.2 H H CH(CH.sub.3)(CH.sub.2).sub.3 2CH.sub.3 4NHCONHCH.     sub.3 60 O O O CH.sub.3 H H CH.sub.2 H 3,4Cl.sub.2 185-187 61 O O O     CH.sub.3 H H CH(CH.sub.3) H 3CF.sub.3 97-99 62 O O O CH(CH.sub.3)CHCH.sub     .2 H H CH(CH.sub.3) H 2,4Cl.sub.2 63 O O S CH.sub.2 CCCH.sub.2 Cl H H     CH(CH.sub.3) H 4OSO.sub.2      CH.sub.3 64 O O O CH.sub.3 H H (CH.sub.2).sub.4 H 2,4,5Cl.sub.3 65 O O     O CH.sub.3 H H CH(CH.sub.3) H 2Cl4F 120-122 66 O O O CH.sub.3 H H     CH(CH.sub.3) 6-OCH.sub.3 2,4Cl.sub.2 141-143  67 O O O CH.sub.3 H H     CH(CH.sub.3) H      ##STR23##      viscous oil  68 O O O CH.sub.2 CCCH.sub.2 OCH.sub.3 H H CH(nC.sub.4     H.sub.9) H 2-COCH.sub.3 69 S O O nC.sub.3 H.sub.7 H H (CH.sub.2).sub.5 H     4SO.sub.2 NHCH.sub.3 70 O O O CH.sub.3 H H CH(CH.sub.3) H 3CH.sub.3 4Cl     136-137 71 O O O CH.sub.3 H H CH(CH.sub.3) H 2,4(CH.sub.3).sub.2 110-112     72 O O O CH(CH.sub.3)CCH H H CH(CH.sub.3) H 2Br 4Cl 73 O O O CH.sub.3 H     H CH(CH.sub.3)CH.sub.2 H 2,4Cl 74 S O O tert. C.sub.4 H.sub.9 H CH.sub.3 C     H(CH.sub.3) H 2,4Cl 149-151 75 O O O cycl. C.sub.5      H.sub.9 H H CH(CH.sub.3) H 2,4Cl.sub.2 76 O O O CH.sub.3 H H C(CH.sub.3)     .sub.2CH.sub.2 H 2,4Cl.sub.2 77 O O O CH.sub.3 H H CH(CH.sub.3) 4CH.sub.3      2,4Cl.sub.2 164-166 78 O O O cycl. C.sub.6 H.sub.11 H H CH(CH.sub.3) H     2,4,5Cl.sub.3 79 O O O CH.sub.3 H H CH(CH.sub.3)(CH.sub.2).sub.2 H     2,4Cl.sub.2 80 O O O CH.sub.3 H H CH(CH.sub.3) H 2,3Cl.sub.2 131-134 81     O O O CH.sub.3 H H CH(CH.sub.3) 2-CH.sub.3 2,4Cl.sub.2  82 O O O     CH.sub.3 H H CH(CH.sub.3) H      ##STR24##      113-115  83 O O O sec. C.sub.4      H.sub.9 H H C(CH.sub.3).sub.2 H 2,4Cl.sub.2 84 O O O tert. C.sub.5     H.sub.11 H H CH(CH.sub.3) H 2CH.sub.3      4Cl 85 O O O CH.sub.3 H H CH(CH.sub.3) H 2,4,6Cl.sub.3 146-148  86 O O     O      ##STR25##      H H CH(CH.sub.3) H 2,4Cl.sub.2 138-140      87 S O O CH.sub.3 H H CH(CH.sub.3)(CH.sub.2).sub.4 H 2,4,5Cl.sub.3 88 O     O S CH.sub.2 CH.sub.2 F H H CH.sub.2 H 4-Cl 89 O O O CH.sub.3 H H     CH(CH.sub.3) H 2,4,5Cl.sub. 3 162-164 90 O O O CH.sub.3 H H CH(CH.sub.3)     H 3,5Cl.sub.2 63-64 91 O O O CH.sub.2 CF.sub.3 H H CH(CH.sub.3) H     2-SO.sub.2      N(CH.sub.3).sub.2 92 O O O CH.sub.3 H H C(CH.sub.3).sub.2(CH.sub.2).sub.     4 H 2,4Br.sub.2 93 O O O CH.sub.2 CH.sub.2 OCH.sub.3 H H CH(CH.sub.3) H     2Br 4Cl 94 O O O CH.sub.3 H H CH(CH.sub.3) H 2,5Cl.sub.2 65-68 95 O O S     CH(CH.sub.3)CH.sub.2 OCH.sub.3 CH.sub.3 CH.sub.3 C(CH.sub.3)(C.sub.2     H.sub.5)(CH.sub.2).sub.2 H 4 F 96 O O S CH.sub.3 H H CH(iC.sub.3     H.sub.7) H 4OCH.sub.3 110-113 97 O O O CH(CH.sub.3)COOC.sub.2 H.sub.5 H     H CH(CH.sub.3) H 2,4Cl.sub.2 viscous oil 98 O O O CH.sub.3 H H CH(CH.sub.     3) H 4NO.sub.2 150-152 99 O O O CH.sub.3 H H  CH(CH.sub.3) H 3 OCH.sub.3     105-107 100 O O O CH.sub.2 CH.sub.2      COOCH.sub.3 H CH.sub.3 CH(CH.sub.3)(CH.sub.2).sub.5 5-CH.sub.3 H 101 O     O O CH.sub.3 H H CH(CH.sub.3) H 4 OCH.sub.3 112-114 102 O O O CH.sub.3 H     H CH(CH.sub.3) H 3 NO.sub.2 60-62 103 O O O cycl. C.sub.7 H.sub.13 H H     CH(CH.sub.3) H 3NHCOOCH.sub.3 104 S O O CH.sub.3 H H CH(CH.sub.3)(CH.sub.     2).sub.5 H 2CH.sub.3 4Cl      105 O O O CH.sub.3 H H CH(CH.sub.3) H     ##STR26##      122-124  106 O O O CH.sub.3 H H CH(CH.sub.3) H 2,4Br.sub.2 141-143 107     O O O CH.sub.3 H H CH(CH.sub.3) H 4-CN 134-136      108 O O O     ##STR27##      H H CH(CH.sub.3) H 2,4Cl.sub.2       109 O O O CH.sub.3 H H (CH.sub.2).sub.6 H 2,4,5Cl.sub.3 110 O O O     CH.sub.3 H H CH(CH.sub.3) H 2CH.sub.3 4Cl 5-isoC.sub.3 H.sub.7 108-110     111 O O S      ##STR28##      H H (CH.sub.2).sub.3 6CH.sub.3 H  112 S O O CH.sub.3 H H CH(CH.sub.3) H     2Br 4Cl 94-96 113 O O O C.sub.2 H.sub.5 H H CH(CH.sub.3) H 2Br 4Cl 84-86     114 O O O CH.sub.3 H H CH(iC.sub.3 H.sub.7) H 2,4Cl.sub.2  115 O O O      ##STR29##      H H CH.sub.2 4 OCH.sub.3 3-Cl      116 O O O CH.sub.3 H H C(CH.sub.3).sub.2(CH.sub.2).sub.5 H 2,4Cl.sub.2     117 O O O CH.sub.3 H H CH(CH.sub.3) H 2,4Cl.sub.2  6CH.sub.3 140-142 118     O O O CH.sub.3 H H CH(nC.sub.3 H.sub.7) H 2,4Cl.sub.2  119 O O O      ##STR30##      H H CH.sub.2 6 OCH.sub.3 H  120 O O O CH.sub.3 H H CH(CH.sub.3) H 2Br     4F 130-132      121 O O O     ##STR31##      CH.sub.2 CH.sub.2 Cl H (CH.sub.2).sub.3 4 Cl H  122 O O O C.sub.2     H.sub.5 H H C(CH.sub.3)(CH.sub.2 CH.sub.2 Cl)(CH.sub.2).sub.2 H 4 Br 123     S O O CH.sub.3 H CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 5 CF.sub.3 3     CF.sub.3 124 O O O CH.sub.3 H H C(CH.sub.3).sub.2(CH.sub.2).sub.2 H     2,4Cl.sub.2      125 O O O     ##STR32##      H H CH(CH.sub.3) H 2,4 Cl.sub. 2 96-98      126 O O O CH.sub.3 H H CH(CH.sub.3) H 2COOCH.sub.3 4Cl 153-155 127 S S     O CH.sub.3 H H CH(CH.sub.3)(CH.sub.2).sub.3 H 4 F 128 O O O i-C.sub.3     H.sub.7 H H CH(CH.sub.3) H 2CH.sub.3 4Cl 145-148 129 O O O CH.sub.3 H H     (CH.sub.2).sub.4 H 2.4 Cl.sub.2 130 O O O CH.sub.3 H H C(CH.sub.2     Cl).sub.2CH.sub.2 H 2CH.sub.3 4Cl 131 O O O CH.sub.3 H H CH(CH.sub.3) H     2 F 103-105 132 O O O CH.sub.3 H CH.sub.2 Cl CH(CH.sub.3) H 2Br 4Cl 133     O O O CH.sub.3 H H CH.sub.2 H 2CH.sub.3 4Cl 173-175 134 O O O C.sub.3 H     H C(CH.sub.3)(CH.sub.2 OCH.sub.3) H 2,4 Cl.sub.2 135 O O O CH.sub.3 H H     CH(CH.sub.3) H 2Cl4NO.sub.2 136 O O O CH.sub.3 H H CH(CH.sub.3) H 3 F     98-100 137 O O O CH.sub.3 H H CH(CH.sub.3) H 2Br 4NO.sub.2 138 O S O     CH.sub.3 H H C(CH.sub.3).sub.2(CH.sub.2).sub.3 H 2,4,5-Cl.sub.3 139 O O     O CH.sub.3 H H (CH.sub.2).sub.6 H 2,4 Cl.sub.2 140 O O O CH.sub.3 H H     CH(CH.sub.3) H 2NO.sub.2 4Cl 199-202 141 O O O CH.sub.3 H H CH(CH.sub.3)     H 2Br 4SCH.sub.3 142 S O O CH.sub.3 H H CH(CH.sub.3) H 2,4Cl.sub.2     112-114 143 O O O CH.sub.3 H H CH(CH.sub.3) H 2CHO 4Cl 170-172 144 O O O     CH.sub.3 H H CH(CH.sub.3) H 2Br 4 OCH.sub.3 145 O O O CH.sub.3 H H     CH(CH.sub.3) 4Cl 2,4 Cl.sub.2 146 O O O CH.sub.3 H H CH(CH.sub.3) H     2Cl-5 OCH.sub.3 133-135 147 O O O CH.sub.3 H H CH(CH.sub.3) H 2Cl-4     SCH.sub.3 148 O O S CH.sub.3 H H CH(CH.sub.3) H 2,4 Cl.sub.2 66-69 149 O     O O CH.sub.3 H H CH.sub.2 H 4 Cl 143-144 150 O O O C.sub.2 H.sub.5 H H     CH(CH.sub.3) H 2CH.sub.3 4Cl 112-114 151 O O O CH.sub.3 H H CH(CH.sub.3)     H 2Cl48SO.sub.2 CH.sub.3 152 O O O CH.sub.3 H H CH(CH.sub.3) H 3,4     Cl.sub.2 106-108 153 O O O CH.sub.3 H H CH(CH.sub.3) 4OCH.sub.3 2,4     Cl.sub.2 154 O O O CH.sub.3 H H CH(CH.sub.3) H 2F5C(CH.sub.3).sub.3 155     O O O CH.sub.3 H H CH(CH.sub.3) H 2,6 Cl.sub.2 156 O O O CH.sub.3 H H     CH(CH.sub.3) H 2,4Cl.sub.2 6F 157 O O O CH.sub.3 H H CH(CH.sub.3) H H     115-117 158 O O O CH.sub. 3 H H CH(CH.sub.3) H 2CH.sub.3 113-116 159 O O     O CH.sub.3 H H CH(CH.sub.3) H 3CN 114-115 160 O O O CH.sub.3 H H     CH(CH.sub.3) H 3CH.sub.3 116-118 161 O O O CH.sub.3 H H CH(CH.sub.3)     6CH.sub.3 2,4 Cl.sub.2 167-169 162 O O O CH.sub.3 H H CH(CH.sub.3) H     3C(CH.sub.3).sub.3 106-108 163 O O O CH.sub.3 H H CH.sub.2).sub.2 H 2,4     Cl.sub.2 162-164 164 O O O CH.sub.3 H H CH(CH.sub.3) H 2CH.sub.2     OCH.sub.3 4Cl      165 O O O CH.sub.3 H H CH(CH.sub.3) H     ##STR33##      155-157  166 O O O CH.sub.3 H H CH(CH.sub.3) 4CH.sub.3 2Br4Cl 123-125     167 O S O CH.sub.3 H H CH(CH.sub.3) H 2,4 Cl.sub.2 168-169 168 O O O     CH.sub.3 H H CH.sub. 2 H 2Br 4Cl 190-192 169 O O O CH.sub.3 H H CH(CH.sub     .3) H 3Cl4F 170 O O O CH.sub.3 H H (CH.sub.2).sub.2 CH(CH.sub.3) H 2,4     Cl.sub.2 171 O O O CH.sub.3 H H C(CH.sub.3)(CH.sub.2).sub.2 H 2,4     Cl.sub.2 172 O O O CH.sub.3 H H CH(CH.sub.3) H 2Cl5CH.sub.3 104-106 173     O O O CH.sub.3 H H CH(CH.sub.3) 5-CF.sub.3 2,4 Cl.sub.2 114-116 174 O O     S CH.sub.3 H H CH.sub.2 H H 105-106 175 O O O CH.sub.3 H H CH(CH.sub.3)     H 2Br5C(CH.sub.3).sub.3 176 O O O CH.sub.3 H H CH(CH.sub.3) H 2CH.sub.3     4,5Cl.sub.2 177 O O O CH.sub.3 H H CH(CH.sub.3) H 2,4Cl.sub.2 5CH.sub.3     178 O O O CH.sub.3 H H CH(CH.sub.3) H 2 Br 89-91 179 O O O CH.sub.3 H H     CH(CH.sub. 3) H 3 Br 127-128 180 O O O CH.sub.3 H H CH(CH.sub.3) H 2I     181 O O O CH.sub.3 H H CH(CH.sub.3) H 3I 182 O O O CH.sub.3 H H CH(CH.sub     .3) H 4I 183 O O O CH.sub.3 H H CH(CH.sub.3) H 2SCN 184 O O O CH.sub.3 H     H CH(CH.sub.3) H 3SCN 185 O O O CH.sub.3 H H CH(CH.sub.3) H 4SCN 186 O O     O CH.sub.3 H H CH(CH.sub.3) H 2,4F.sub.2 187 O O O CH.sub.3 H H CH(CH.sub     .3) H 2F4Cl 119-122 188 O O O CH.sub.3 H H CH(CH.sub.3) H 2F4Br 189 O O     O CH.sub.3 H H CH(CH.sub.3) H 2I4Cl 190 O O O CH.sub.3 H H CH(CH.sub.3)     H 2Cl4CH.sub.3 191 O O O CH.sub.3 H H CH(CH.sub.3) H 2Br4CH.sub.3     120-122 192 O O O CH.sub.3 H H CH(CH.sub.3) H 2Cl4CF.sub.3 193 O O O     CH.sub.3 H H CH(CH.sub.3) H 4CF.sub.3 103-105 194 O O O CH.sub.3 H H     CH(CH.sub.3) H 3OCHF.sub.2 195 O O O CH.sub.3 H H CH(CH.sub.3) H     3OCF.sub.2 CHF.sub.2 196 O O O CH.sub.3 H H CH(CH.sub.3) H 3C.sub.2     H.sub.5 197 O O O CH.sub.3 H H CH(CH.sub.3) H 2,5(CH.sub.3).sub.2 4Cl     198 O O O CH.sub.3 H H CH(CH.sub.3) H 2,6Cl.sub.2 4CF.sub.3 199 O O O     CH.sub.3 H H CH(CH.sub.3) H 2,3,4,5,6Cl.sub.5 200 O O O CH.sub.3 H H     CH(CH.sub.3) H 2,4Cl.sub.2 3CH.sub.3 201 O O O CH.sub.3 H H CH(CH.sub.3)     4F 2,4Cl.sub.2 202 O O O CH(CH.sub.2 F).sub.2 H H CH(CH.sub.3) H     2,4Cl.sub.2 144-146 203 O O O CH.sub.3 H H CH(CH.sub.3 ) H 2CF.sub.3     98-99 204 S O O C.sub.2 H.sub.5 H H CH(CH.sub.3) H 2,4Cl.sub.2 106-109     205 O O O CH.sub.3 H H CH(CH.sub.3) H 4CH.sub.3 118-121 206 O O O     CH.sub.3 H H (CH.sub.2).sub.2 H 4Cl 160-162 207 S O O CH.sub.3 H H     CH(CH.sub.3) H 2Cl 110-112 208 S O O CH.sub.3 H H CH(CH.sub.3) H 3Br     112-114 209 S O O CH.sub.3 H H CH(CH.sub.3) H 2Br 210 O O O CH.sub.3 H H (     CH.sub.2).sub.2 H 3NO.sub.2 140-142 211 O O O CH.sub.3 H H CH(CH.sub.3)     H 2NO.sub.2 152-154 212 O O O i-C.sub.3 H.sub.7 H H CH(CH.sub.3) H     2,5Cl.sub.2 144-146 213 O O O i-C.sub.3 H.sub.7 H H CH(CH.sub.3) H 2Br     214 O O O C.sub.2 H.sub.5 H H CH(CH.sub.3)  H 2Br 215 S O O CH.sub.3 H H C     H(CH.sub.3) H 2,5Cl.sub.2 121-123 216 O O O CH.sub.3 H H CH(CH.sub.3) H     2Br4CF.sub.3 144-146 217 O O O CH.sub.3 H H CH(CH.sub.3) H 2Cl4 viscous     oil 218 O O O CH.sub.3 H H CH(CH.sub.3) H 3NO.sub.2 4CF.sub.3 144-146     219 O O O CH.sub.3 H H CH(CH.sub.3) H 2Cl4,5(CH.sub.3).sub.2 128-130 220     O O O i-C.sub.3 H.sub.7 H H CH(CH.sub.3) H 2,4,5Cl.sub.3 126-127 221 O O     O C.sub.2 H.sub.5 H H CH(CH.sub.3) H 2,5Cl.sub.2 120-122 222 O O O     C.sub.2 H.sub.5 H H CH(CH.sub.3) H 2Cl 223 O O O C.sub.2 H.sub.5 H H     CH(CH.sub.3) H 3Br 224 O O O C.sub.2      H.sub.5 H H CH(CH.sub.3) H 2,4,5Cl.sub.3 129-131 225 O O O C.sub.2     H.sub.5 H H CH(CH.sub.3) H 2Cl4Br 226 S O O CH.sub.3 H H CH(CH.sub.3) H     2,4,5Cl.sub.3 177-179 227 O O O i-C.sub.3 H.sub.7 H H CH(CH.sub.3) H     2Cl4Br 228 O O O C.sub.2 H.sub.5 H H CH(CH.sub.3) H 2Cl4F 229 O O O     i-C.sub.3      H.sub.7 H H CH(CH.sub.3) H 2Cl4F

The compounds of the invention can be converted into the conventionalformulations, e.g. solutions, emulsions, suspensions, dusts, powders,pastes and granules. The form of application depends entirely on thepurpose for which the agents are being used; it should, however, ensurea fine and uniform distribution of the active ingredient. Theformulations are prepared in the conventional manner, for example bydiluting the active ingredient with solvent and/or carriers, with orwithout the addition of emulsifiers and dispersants and, where water isused as the diluent, with or without organic auxiliary solvents.Suitable auxiliaries are, essentially, solvents, for example aromatics,e.g., xylene and benzene, chloroaromatics, e.g. chlorobenzene,paraffins, e.g. petroleum fractions, alcohols, e.g. methanol andbutanol, amines, e.g., ethanolamine, dimethylformamide, and water; solidcarriers, for example natural rock powders, e.g. kaolin, alumina, talcand chalk, and synthetic rock powders, e.g. highly disperse silica andsilicates; emulsifiers, for example non-ionic and anionic emulsifiers,e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates, and dispersants, for example lignin, sulfite wasteliquors and methylcellulose.

The agent in general contain from 0.1 to 95% by weight of activeingredient, preferably from 0.5 to 90%.

The agents, and the ready-to-use preparations obtained therefrom, e.g.,solutions, emulsions, suspensions, powders, dusts, pastes or granules,are applied in conventional manner, e.g. by spraying, atomizing,dusting, broadcasting or watering.

EXAMPLES ILLUSTRATING THE HERBICIDAL ACTION

The influence of various representatives of the compounds according tothe invention on the growth of unwanted and crop plants in comparisonwith chemically similar, prior art compounds is demonstrated in thefollowing greenhouse experiments.

The vessels employed were plastic flowerpots having a volume of 300 cm³,and which were filled with a sandy loam containing about 1.5% humus. Theseeds of the test plants (cf. Table 1) were sown shallow, andseparately, according to species. For the preemergence treatment, theactive ingredients were applied to the surface of the soil immediatelyafter the seeds had been sown. The compounds were emulsified orsuspended in water as vehicle, and sprayed through finely distributingnozzles. After the agents had been applied, the vessels were lightlysprinkler-irrigated to induce germination and growth and to activate thechemical agents. Transparent plastic covers were then placed on thevessels until the plants had taken root. The cover ensured uniformgermination of the plants, insofar as this was not impaired by thechemicals.

For the postemergence treatment, the plants were first grown in thevessels to a height of from 3 to 10 cm, depending on growth form, beforebeing treated. No cover was placed on the vessels.

The pots were set up in the greenhouse-species from warmer areas at from25° to 40° C., and species from moderate climates at 15° to 30° C. Theexperiments were run for from 3 to 6 weeks. During this period, theplants were tended and their reactions to the various treatmentsassessed. The following tables contain the compounds investigated, theapplication rates in kg/ha of active ingredient, and the plants used forthe tests. The scale used for assessment was 0 to 100, 0 denoting nodamage or normal emergence, and 100 denoting nonemergence or completedestruction of at least the visible plant parts.

The following tables demonstrate the selective herbicidal action of thecompounds according to the invention. The agents may be applied pre- orpostemergence, either to the location before the unwanted plants havegerminated or sprouted from vegetative plant parts, or to the leaves ofthe unwanted and crop plants. A further application technique is tospray the active ingredients with the aid of spraying equipment in sucha way that the leaves of sensitive crop plants are if possible not hit;the active ingredients reach the soil or unwanted plants growing belowthe crop plants (post-directed, lay-by treatment). The application ratesvary, depending on season and growth stage, from 0.1 to 15 kg/ha andmore; higher rates are particularly suitable for total elimination ofvegetation.

In view of the many application methods possible, the agents accordingto the invention, or mixtures containing them, may be used in additionto the crop plants listed in the tables in a large number of other cropsfor eliminating unwanted growth.

The following crop plants are given by way of example:

    ______________________________________                                        Botanical name      Common name                                               ______________________________________                                        Allium cepa         onions                                                    Ananas comosus      pineapples                                                Arachis hypogaea    peanuts (groundnuts)                                      Asparagus officinalis                                                                             asparagus                                                 Aventa sativa       oats                                                      Beta vulgaris spp. altissima                                                                      sugarbeets                                                Beta vulgaris spp. rapa                                                                           fodder beets                                              Beta vulgaris spp. esculenta                                                                      table beets, red beets                                    Brassica napus var. napus                                                                         rape                                                      Brassica napus var. napobrassica                                              Brassica napus var. rapa turnips                                              Brassica rapa var. silvestris                                                 Camellia sinensis   tea plants                                                Carthamus tinctorius                                                                              safflower                                                 Carya illinoinensis pecan trees                                               Citrus limon        lemons                                                    Citrus maxima       grapefruits                                               Citrus reticulata                                                             Citrus sinensis     orange trees                                              Coffea arabica (Coffea canephora,                                             Coffea liberica)    coffee plants                                             Cucumis melo        melons                                                    Cucumis sativus     cucumbers                                                 Cynodon dactylon    Bermudagrass in turf                                                          and lawns                                                 Daucus carota       carrots                                                   Elais guineensis    oil palms                                                 Fragaria vesca      strawberries                                              Glycine max         soybeans                                                  Gossypium hirsutum                                                            (Gossypium arboreum cotton                                                    Gessypium herbaceum                                                           Gossypium vitifolium)                                                         Helianthus annuus   sunflowers                                                Helianthus tuberosus                                                          Hevea brasiliensis  rubber plants                                             Hordeum vulgare     barley                                                    Humulus lupulus     hops                                                      Ipomoea batatas     sweet potatoes                                             Juglans regia      walnut trees                                              Lactuca sativa      lettuce                                                   Lens culinaris      lentils                                                   Linum usitatissimum flax                                                      Lycopersicon lycopersicum                                                                         tomatoes                                                  Malus spp.          apple trees                                               Manihot esculenta   cassava                                                   Medicago sativa     alfalfa (lucerne)                                         Mentha piperita     peppermint                                                Musa spp.           banana plants                                             Nicothiana tabacum  tobacco                                                   (N. rustica)                                                                  Olea europaea       olive trees                                               Oryza sativa        rice                                                      Panicum miliaceum                                                             Phaseolus lunatus   limabeans                                                 Phaseolus mungo     mungbeans                                                 Phaseolus vulgaris  snapbeans, green beans,                                                       dry beans                                                 Pennisetum glaucum                                                            Petroselinum crispum                                                                              parsley                                                   spp. tuberosum                                                                Picea abies         Norway spruce                                             Abies alba          fir                                                       Pinus spp.          pine trees                                                Pisum sativum       English peas                                              Prunus avium        cherry trees                                              Prunus domestica    plum trees                                                Prunus dulcis       almond trees                                              Prunus persica      peach trees                                               Pyrus communis      pear trees                                                Ribes sylvestre     redcurrants                                               Ribes uva-crispa                                                              Ricinus communis                                                              Saccharum officinarum                                                                             sugar cane                                                Secale cereale      rye                                                       Sesamum indicum     sesame                                                    Solanum tuberosum   Irish potatoes                                            Sorghum bicolor (s. vulgare)                                                                      grain sorghum                                             Sorghum dochna                                                                Spinacia oleracea   spinach                                                   Theobroma cacao     cacao plants                                              Trifolium pratense  red clover                                                Triticum aestivum   wheat                                                     Vaccinium corymbosum                                                                              blueberries                                               Vaccinium vitis-idaea                                                                             cranberries                                                Vicia faba         tick beans                                                Vigna sinensis (V. unguicculata)                                                                  cow peas                                                  Vitis vinifera      grapes                                                    Zea mays            Indian corn, sweet corn,                                                      maize                                                     ______________________________________                                    

The new m-anilide-urethanes may be mixed with each other and withnumerous representatives of other herbicidal or growth-regulating activeingredient groups. Examples of suitable components for mixtures arediazines, N-phenylcarbamates, thiolcarbamates, diurethanes,halocarboxylic acids, phenoxy fatty acids, triazines, amides, ureas,diphenyl ethers, triazinones, uracils, benzofuran derivatives, etc.These combinations broaden the spectrum of action and in some instancessynergistic effects are achieved. A number of active ingredients which,when combined with the new active ingredients, give mixtures suitablefor widely varying areas of application are given below by way ofexample:

    ______________________________________                                         ##STR34##                                                                    R                 R.sup.1      R.sup.2                                        ______________________________________                                         ##STR35##        NH.sub.2     Cl                                              ##STR36##        NH.sub.2     Br                                              ##STR37##        OCH.sub.3    OCH.sub.3                                       ##STR38##                                                                                       ##STR39##   Cl                                              ##STR40##        OCH.sub.3    OCH.sub.3                                       ##STR41##        NH.sub.2     Cl                                              ##STR42##                                                                                       ##STR43##   Cl                                              ##STR44##        NHCH.sub.3   Cl                                              ##STR45##        OCH.sub.3    Cl                                              ##STR46##        NH.sub.2     Br                                              ##STR47##        OCH.sub.3    OCH.sub.3                                       ##STR48##        NH.CH.sub.3  Cl                                             ______________________________________                                         ##STR49##                                                                    R             R.sup.1   R.sup.2  R.sup.3                                      ______________________________________                                                       ##STR50##                                                                              H        H (salts)                                    H                                                                                            ##STR51##                                                                              H        CH.sub.3 (salts)                             H                                                                                            ##STR52##                                                                              H        Cl (salts)                                   CH.sub.2OCH.sub.3                                                                            ##STR53##                                                                              H        H                                            H                                                                                            ##STR54##                                                                              H        F (salts)                                    CH.sub.2OCH.sub.3                                                                            ##STR55##                                                                              H        Cl                                           CH.sub.2OCH.sub.3                                                                            ##STR56##                                                                              H        F                                            CN                                                                                           ##STR57##                                                                              H        Cl                                           ______________________________________                                         ##STR58##                                                                    R     R.sup.1   R.sup.2 R.sup.3     R.sup.4                                   ______________________________________                                        H     H.sub.3 CSO.sub.2                                                                       H       n.C.sub.3 H.sub.7                                                                         n.C.sub.3 H.sub.7                         H     F.sub.3 C H       C.sub.2 H.sub.5                                                                           C.sub.4 H.sub.9                           H     F.sub.3 C H       n.C.sub.3 H.sub.7                                                                         n.C.sub.3 H.sub.7                         H     F.sub.3 C H       CH.sub.2CH.sub.2 Cl                                                                       n.C.sub. 3 H.sub.7                        H     tert.C.sub.4 H.sub.9                                                                    H       sec.C.sub.4 H.sub.9                                                                       sec.C.sub.4 H.sub.9                       H     SO.sub.2 NH.sub.2                                                                       H       n.C.sub.3 H.sub.7                                                                         n.C.sub.3 H.sub.7                         H     F.sub.3 C H       n.C.sub.3 H.sub.7                                                                          ##STR59##                                H.sub.3 C                                                                           H.sub.3 C H       H           sec.C.sub.4 H.sub.9                       H.sub.3 C                                                                           H.sub.3 C H       H                                                                                          ##STR60##                                H     F.sub.3 C NH.sub.2                                                                              n.C.sub.3 H.sub.7                                                                         n.C.sub.3 H.sub.7                         H     H.sub.3 C H       n.C.sub.3 H.sub.7                                                                         n.C.sub.3 H.sub.7                         H     iC.sub.3 H.sub.7                                                                        H       n.C.sub.3 H.sub.7                                                                         n.C.sub.3 H.sub.7                         ______________________________________                                         ##STR61##                                                                    R               R.sup.1                                                                              R.sup.2                                                ______________________________________                                         ##STR62##      H      iC.sub.3 H.sub.7                                       CH.sub.3        H                                                                                     ##STR63##                                              ##STR64##      H                                                                                     ##STR65##                                              ##STR66##      H      CH.sub.2CCCH.sub.2 Cl                                   ##STR67##      H      iC.sub.3 H.sub.7                                        ##STR68##      H                                                                                     ##STR69##                                              ##STR70##      H      CH.sub.3                                                ##STR71##      H      CH.sub.3                                               CH.sub.3        H                                                                                     ##STR72##                                              ##STR73##      H                                                                                     ##STR74##                                             ______________________________________                                         ##STR75##                                                                    R                 R.sup.1     R.sup.2                                         ______________________________________                                         ##STR76##        H           CH.sub.3                                         ##STR77##        H           C.sub.2 H.sub.5                                  ##STR78##        H           C.sub.2 H.sub.5                                  ##STR79##        CH.sub.3    CH.sub.3                                         ##STR80##        H           CH.sub.3                                         ##STR81##        H           C.sub.2 H.sub.5                                  ##STR82##        H           C.sub.2 H.sub.5                                  ##STR83##        H           CH.sub.3                                         ##STR84##        H           CH.sub.3                                         ##STR85##                                                                    ______________________________________                                         ##STR86##                                                                    R            R.sup.1     R.sup.2                                              ______________________________________                                        iC.sub.3 H.sub.7                                                                           iC.sub.3 H.sub.7                                                                          CH.sub.2CClCCl.sub.2                                 iC.sub.3 H.sub.7                                                                           iC.sub.3 H.sub.7                                                                          CH.sub.2CClCHCl                                      n.C.sub.3 H.sub.7                                                                          n.C.sub.3 H.sub.7                                                                         C.sub.2 H.sub.5                                       ##STR87##   C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                      sec.C.sub.4 H.sub.9                                                                        sec.C.sub.4 H.sub.9                                                                       C.sub.2 H.sub.5                                      n.C.sub.3 H.sub.7                                                                          n.C.sub.3 H.sub.7                                                                         n.C.sub.3 H.sub.7                                    C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                            ##STR88##                                           sec.C.sub.4 H.sub.9                                                                        sec.C.sub.4 H.sub.5                                                                        ##STR89##                                            ##STR90##   C.sub.2 H.sub.9                                                                           C.sub.2 H.sub.5                                      iC.sub.3 H.sub.7                                                                           iC.sub.3 H.sub.7                                                                           ##STR91##                                           iC.sub.3 H.sub.7                                                                           iC.sub.3 H.sub.7                                                                           ##STR92##                                           ______________________________________                                         ##STR93##                                                                              R                                                                   ______________________________________                                                  CH.sub.2CClCHCl                                                               CH.sub.2CClCCl.sub.2                                                           ##STR94##                                                          ______________________________________                                                   ##STR95##                                                          R                  X     Y      R.sup.1                                       ______________________________________                                        CH.sub.3           Cl    Cl     Na                                             ##STR96##         Cl    H      CH.sub.3                                       ##STR97##         H     H      H (salts)                                     Cl                 Cl    Cl     Na                                             ##STR98##         H     CH.sub.3                                                                             CH.sub.3                                       ##STR99##         H     CH.sub.3                                                                             C.sub.2 H.sub.5                               C.sub.2 H.sub.5    Cl    Cl     Na                                             ##STR100##        H     CH.sub.3                                                                             iC.sub.3 H.sub.7                               ##STR101##        H     CH.sub.3                                                                             CH.sub.3                                       ##STR102##        H     CH.sub.3                                                                              ##STR103##                                    ##STR104##        H     CH.sub.3                                                                             Na                                             ##STR105##        H     CH.sub.3                                                                             Na                                             ##STR106##        H     CH.sub.3                                                                             CH.sub.3                                      ______________________________________                                         ##STR107##                                                                   R     R.sup.1    X       R.sup.2                                                                             R.sup.3                                        ______________________________________                                        H     tert.C.sub.4 H.sub.9                                                                     SCH.sub.3                                                                             H     C.sub.2 H.sub.5                                H     C.sub.2 H.sub.5                                                                          SCH.sub.3                                                                             H     C.sub.2 H.sub.5                                H     iC.sub.3 H.sub.7                                                                         SCH.sub.3                                                                             H     C.sub.2 H.sub.5                                H     CH.sub.3   SCH.sub.3                                                                             H     iC.sub.3 H.sub.7                               H     iC.sub.3 H.sub.7                                                                         Cl      H     C.sub.2 H.sub.5                                H     iC.sub.3 H.sub.7                                                                         Cl      H                                                                                    ##STR108##                                    H     C.sub.2 H.sub.5                                                                          Cl      H     C.sub.2 H.sub.5                                H     C.sub.2 H.sub.5                                                                          Cl      H                                                                                    ##STR109##                                    H     iC.sub.3 H.sub.7                                                                         Cl      H     iC.sub.3 H.sub.7                               H     iC.sub.3 H.sub.7                                                                         OCH.sub.3                                                                             H     iC.sub.3 H.sub.7                                      ##STR110##                                                                              Cl      H                                                                                    ##STR111##                                    H     C.sub.2 H.sub.5                                                                          Cl      H                                                                                    ##STR112##                                    H     C.sub.2 H.sub.5                                                                          Cl      H                                                                                    ##STR113##                                    ______________________________________                                         ##STR114##                                                                   R         R.sup.1          R.sup.2                                            ______________________________________                                        CH.sub.3  CH.sub.3         CH(C.sub.6 H.sub.5).sub.2                           ##STR115##                                                                             H                                                                                               ##STR116##                                         ##STR117##                                                                             H                                                                                               ##STR118##                                         ##STR119##                                                                             H                C.sub.2 H.sub.5                                     ##STR120##                                                                             H                C.sub.2 H.sub.5                                     ##STR121##                                                                             H                                                                                             ##STR122##                                           ##STR123##                                                                              ##STR124##      CH.sub.2 Cl                                         ##STR125##                                                                              ##STR126##      CH.sub.2 Cl                                         ##STR127##                                                                             CH.sub.2OCH.sub.3                                                                              CH.sub.2 Cl                                         ##STR128##                                                                              ##STR129##      CH.sub.2 Cl                                         ##STR130##                                                                             iC.sub.3 H.sub.7 CH.sub.2 Cl                                         ##STR131##                                                                              ##STR132##      CH.sub.2 Cl                                         ##STR133##                                                                             CH.sub.2OC.sub.4 H.sub.9 n.                                                                    CH.sub.2 Cl                                         ##STR134##                                                                             CH.sub.2OC.sub.2 H.sub.5                                                                       CH.sub.2 Cl                                         ##STR135##                                                                              ##STR136##      CH.sub.2 Cl                                         ##STR137##                                                                             CH.sub.2CH.sub.2OCH.sub.3                                                                      CH.sub.2 Cl                                         ##STR138##                                                                              ##STR139##      CH.sub.2 Cl                                         ##STR140##                                                                              ##STR141##      CH.sub.2 Cl                                         ##STR142##                                                                              ##STR143##      CH.sub.2 Cl                                         ##STR144##                                                                              ##STR145##      CH.sub.2 Cl                                        CH.sub.3  CH.sub.3                                                                                        ##STR146##                                        C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                                 ##STR147##                                        CH.sub.2CHCH.sub.2                                                                         CH.sub.2CHCH.sub.2                                                                          CH.sub.2 Cl                                         ##STR148##  H                                                                                            ##STR149##                                         ##STR150##  H             CH.sub.3                                            ##STR151##  H             CH.sub.3                                           ______________________________________                                         ##STR152##                                                                   X           Y         R                                                       ______________________________________                                        Br          Br        H (salts)                                               I           I         H (salts)                                               Br          Br                                                                                       ##STR153##                                              ##STR154##             salts, esters                                          ##STR155##             salts, esters                                         ______________________________________                                         ##STR156##                                                                   R              R.sup.1                                                                              R.sup.2   R.sup.3                                       ______________________________________                                         ##STR157##    H      CH.sub.3  CH.sub.3                                       ##STR158##    H      CH.sub.3  CH.sub.3                                       ##STR159##    H      CH.sub.3  CH.sub.3                                       ##STR160##    H      CH.sub.3  H                                              ##STR161##    CH.sub.3                                                                             CH.sub. 3 H                                              ##STR162##    H      CH.sub.3  CH.sub.3                                       ##STR163##    H      CH.sub.3  CH.sub.3                                       ##STR164##    H                                                                                     ##STR165##                                                                             H                                              ##STR166##    H      CH.sub.3  CH.sub.3                                       ##STR167##    H      CH.sub.3                                                                                 ##STR168##                                    ##STR169##    H      CH.sub.3  OCH.sub.3                                      ##STR170##    H      CH.sub.3  CH.sub.3                                       ##STR171##    H                                                                                     ##STR172##                                                                             H                                              ##STR173##    H      CH.sub.3  OCH.sub.3                                      ##STR174##    H      CH.sub.3  CH.sub.3                                       ##STR175##    H      CH.sub.3  CH.sub.3                                       ##STR176##    H      CH.sub.3  CH.sub.3                                       ##STR177##    H      CH.sub.3  CH.sub.3                                       ##STR178##    H      CH.sub.3  OCH.sub.3                                      ##STR179##    H      CH.sub.3  OCH.sub.3                                      ##STR180##    H      CH.sub.3  H                                              ##STR181##    CH.sub.3                                                                             CH.sub.3  H                                              ##STR182##    CH.sub.3                                                                             CH.sub.3  H                                              ##STR183##    H      C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                ##STR184##    H      CH.sub.3  CH.sub.3                                       ##STR185##    H      CH.sub.3  OCH.sub.3                                      ##STR186##    H      CH.sub.3  CH.sub.3                                       ##STR187##                                                                   ______________________________________                                         ##STR188##                                                                   R          R.sup.1   R.sup.2  R.sup.3                                         ______________________________________                                        Cl         Cl        Cl       H                                               F          Cl        Cl       H                                               NO.sub.2   CF.sub.3  H        H                                               Cl         CF.sub.3  H        COOH (salts)                                    Cl         Cl        H        H                                               Cl         Cl        H        OCH.sub.3                                       Cl         Cl        H                                                                                       ##STR189##                                     H          CF.sub.3  Cl       H                                               H          CF.sub.3  Cl       OC.sub.2 H.sub.5                                ______________________________________                                         ##STR190##                                                                   R           R.sup.1            R.sup.2                                        ______________________________________                                        tert.C.sub.4 H.sub.9                                                                      NH.sub.2           SCH.sub.3                                      tert.C.sub.4 H.sub.9                                                                       ##STR191##        SCH.sub.3                                       ##STR192## NH.sub.2           CH.sub.3                                       ______________________________________                                         ##STR193##                                                                   R          R.sup.1   R.sup.2  R.sup.3                                         ______________________________________                                        H          CH.sub.3  Br                                                                                      ##STR194##                                     H          CH.sub.3  Br       iC.sub.3 H.sub.7                                H          CH.sub.3  Cl       tert.C.sub.4 H.sub.9                            H          CH.sub.3  Cl                                                                                      ##STR195##                                      ##STR196##                                                                   ______________________________________                                         ##STR197##                                                                   R           R.sup.1    R.sup.2  R.sup.3                                       ______________________________________                                         ##STR198## sec.C.sub.4 H.sub.9                                                                      H        H                                             H           CH.sub.3   H        H (salts, esters)                             H           sec.C.sub.4 H.sub.9                                                                      H        H (salts, esters)                              ##STR199## tert.C.sub.4 H.sub.9                                                                     H        H                                              ##STR200## tert.C.sub.4 H.sub.9                                                                     H        CH.sub.3                                      H           iC.sub.3 H.sub.7                                                                         CH.sub.3 H (salts, esters)                             H           tert.C.sub.4 H.sub.9                                                                     H        H (salts)                                     ______________________________________                                         ##STR201##                                                                   X                Y           R                                                ______________________________________                                        CF.sub.3         H           CH.sub.3                                         H                F           CH.sub.3                                          ##STR202##                                                                   ______________________________________                                         ##STR203##                                                                   R                       R.sup.1                                               ______________________________________                                        CH.sub.3                C.sub.2 H.sub.5                                        ##STR204##             C.sub.2 H.sub.5                                        ##STR205##             C.sub.2 H.sub.5                                       ______________________________________                                         ##STR206##                                                                   R                        R.sup.1                                              ______________________________________                                         ##STR207##              CH.sub.3                                              ##STR208##              CH.sub.3                                              ##STR209##              CH.sub.3                                             ______________________________________                                         ##STR210##                                                                   R        R.sup.1  R.sup.2  X                                                  ______________________________________                                        CH.sub.3 CH.sub.3 H                                                                                       ##STR211##                                        CH.sub.3 CH.sub.3 Br       CH.sub.3 OSO.sub.2 O                               CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.2 OSO.sub.2O                                CH.sub.3 CH.sub.3 CH.sub.3 CF.sub.3SO.sub.2                                    ##STR212##                                                                    ##STR213##                                                                    ##STR214##                                                                    ##STR215##                                                                    ##STR216##                                                                   ______________________________________                                         ##STR217##                                                                   R       R.sup.1 R.sup.2  R.sup.3                                                                             R.sup.4                                        ______________________________________                                        Cl      Cl      NH.sub.2 Cl    COOH (salts, esters)                            ##STR218##                                                                    ##STR219##                                                                    ##STR220##                                                                    ##STR221##                                                                    ##STR222##                                                                    ##STR223##                                                                    ##STR224##                                                                    ##STR225##                                                                   ______________________________________                                         ##STR226##                                                                   R       R.sup.1 R.sup.2  R.sup.3 R.sup.4                                      ______________________________________                                        H       Cl      NH.sub.2 Cl      H (salts, esters,                                                             amides)                                      Cl      Cl      H        Cl      Na                                           H       I       I        I       H                                            Cl      H       Cl       OCH.sub.3                                                                             H                                            Cl      Cl      H        Cl      H.(CH.sub.3).sub.2 NH                        ______________________________________                                         ##STR227##                                                                   R            R.sup.1  R.sup.2                                                 ______________________________________                                         ##STR228##  CH.sub.3 H       salts, esters, amides                            ##STR229##  H        H       salts, esters, amides                            ##STR230##  H        H       salts, esters, amides                            ##STR231##  H        H       salts, esters, amides                            ##STR232##  CH.sub.3 H       salts, esters, amides                            ##STR233##  CH.sub.3 H       salts, esters, amides                            ##STR234##                                                                    ##STR235##          salts, esters, amides                                     ##STR236##          salts, esters, amides                                     ##STR237##          salts, esters, amides                                    ______________________________________                                         ##STR238##                                                                   R               R.sup.1      R.sup.2                                          ______________________________________                                        OH              CH.sub.3     Na                                               CH.sub.3        CH.sub.3     Na                                               CH.sub.3        CH.sub.3     OH                                               ONa             CH.sub.3     Na                                               ______________________________________                                         ##STR239##                                                                   R           R.sup.1        R.sup.2                                            ______________________________________                                         ##STR240## CH.sub.2OC.sub.2 H.sub.5                                                                     CH.sub.3                                            ##STR241## CH.sub.2OC.sub.3 H.sub.7 i                                                                   CH.sub.3                                            ##STR242## CH.sub.2O C.sub.2 H.sub.5                                                                    CH.sub.3                                            ##STR243## C.sub.3 H.sub.7 i                                                                            NHCH.sub.3                                          ##STR244##                                                                    ##STR245##                                                                    ##STR246##                                                                    ##STR247##                                                                    ##STR248##            (salts)                                                 ##STR249##            (salts, esters)                                         ##STR250##                                                                    ##STR251##                                                                    ##STR252##            (salts)                                                 ##STR253##                                                                    ##STR254##                                                                    ##STR255##            and other salts                                         ##STR256##                                                                    ##STR257##                                                                    ##STR258##                                                                    ##STR259##            (salts)                                                 ##STR260##                                                                   NH.sub.4 SCN                                                                   ##STR261##                                                                    ##STR262##                                                                    ##STR263##            (salts)                                                 ##STR264##                                                                    ##STR265##                                                                    ##STR266##                                                                    ##STR267##                                                                    ##STR268##                                                                    ##STR269##            salts, esters, amides                                   ##STR270##                                                                    ##STR271##                                                                    ##STR272##                                                                    ##STR273##                                                                   ______________________________________                                    

It may also be useful to apply the new compounds, either alone or incombination with other herbicides, in admixture with other cropprotection agents, e.g., agents for combating pests or phytopathogenicfungi or bacteria. The compounds may also be mixed with solutions ofmineral matters used to remedy nutritional or trace elementdeficiencies. Oils of various types, wetting agents, spreader-stickersand antifoams may also be added to the individual active ingredients ormixtures thereof.

                  TABLE 1                                                         ______________________________________                                        List of plant names                                                           Botanical name  Common name                                                   ______________________________________                                        Amaranthus retroflexus                                                                        redroot pigweed                                               Arachys hypogaea                                                                              peanuts (groundnuts)                                          Beta vulgaris   sugarbeets                                                    Cassia tora                                                                   Centaurea cyanus                                                                              cornflower                                                    Chenopodium album                                                                             lambsquarters (goosefoot)                                     Cyperus ferax                                                                 Echinochloa crus galli                                                                        barnyardgrass                                                 Euphorbia geniculata                                                                          South American member of the                                                  spurge family                                                 Glycine max     soybeans                                                      Gossypium hirsutum                                                                            cotton                                                        Hordeum vulgare barley                                                        Ipomoea spp.    morningglory                                                  Lamium spp.     dead-nettle                                                   Matricaria spp. chamomille                                                    Oryza sativa    rice                                                          Polygonum persicaria                                                                          ladysthumb                                                    Sesbania exaltata                                                                             hemp sesbania (coffeeweed)                                    Sinapis alba    white mustard                                                 Sorghum bicolor wild cane (grain sorghum)                                     Triticum aestivum                                                                             wheat                                                         Zea mays        Indian corn                                                   Mentha piperita peppermint                                                    Galium aparine  catchweed bedstraw                                            ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                        Herbicidal action of the novel compounds on preemergence                      application in the greenhouse                                                 Compound             Test plant: Sinapis alba                                 no.          kg/ha   % damage                                                 ______________________________________                                        157          3.0     100                                                      57           3.0     80                                                       1            3.0     100                                                      149          3.0     90                                                       5            3.0     90                                                       40           3.0     100                                                      3            3.0     100                                                      6            3.0     100                                                      41           3.0     90                                                       12           3.0     100                                                      32           3.0     80                                                       38           3.0     100                                                      28           3.0     100                                                      60           3.0     100                                                      17           3.0     90                                                       89           3.0     90                                                       53           3.0     90                                                       65           3.0     90                                                       52           3.0     90                                                       70           3.0     80                                                       133          3.0     100                                                      4            3.0     100                                                      71           3.0     90                                                       61           3.0     100                                                      120          3.0     100                                                      117          3.0     90                                                       2            3.0     100                                                      168          3.0     90                                                       99           3.0     90                                                       94           3.0     90                                                       150          3.0     90                                                       128          3.0     90                                                       36           3.0     100                                                      193          3.0     100                                                      131          3.0     100                                                      178          3.0     100                                                      179          3.0     100                                                      136          3.0     100                                                      152          3.0     100                                                      202          3.0     90                                                       113          3.0     100                                                      172          3.0     90                                                       158          3.0     100                                                      160          3.0     100                                                      205          3.0     90                                                       66           3.0     80                                                       15           3.0     90                                                       112          3.0     90                                                       142          3.0     100                                                      204          3.0     80                                                       ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                        Herbicidal action of the novel compounds on postemergence                     treatment in the greenhouse                                                                   Test plants and % damage                                      Compound              Centaurea  Ipomea                                       no.       kg/ha       cyanus     spp.                                         ______________________________________                                        57        3.0         90         100                                          1         3.0         100        100                                          85        3.0         70         100                                          17        3.0         90         90                                           89        3.0         100        100                                          53        3.0         100        100                                          65        3.0         90         100                                          58        3.0         100        100                                          50        3.0         100        100                                          70        3.0         60         90                                           71        3.0         90         100                                          61        3.0         60         100                                          67        3.0         90         100                                          82        3.0         --         100                                          106       3.0         100        100                                          120       3.0         100        100                                          90        3.0         100        90                                           94        3.0         100        100                                          119       3.0         --         100                                          168       3.0         --         100                                          159       3.0         100        60                                           179       3.0         100        100                                          136       3.0         100        100                                          97        3.0         80         100                                          125       3.0         100        90                                           191       3.0         100        --                                           160       3.0         100        70                                           146       3.0         90         80                                           204       3.0         100        --                                           193       3.0         100        100                                          187       3.0         100        100                                          218       3.0         100        90                                           216       3.0         100        100                                          217       3.0         90         80                                           ______________________________________                                    

                                      TABLE 4                                     __________________________________________________________________________    Selective control of unwanted plants in soybeans and cotton;                  postemergence treatment in the greenhouse                                                                    Test plants and % damage                                                          Goosy-  Amaran-   Euphor-                                                 Gly-                                                                              pium-   thus-                                                                              Cheno-                                                                             bia                                                     cine                                                                              hirsu-                                                                            Oryza                                                                             retro-                                                                             podium-                                                                            genicu-                                                                            Sesbania            Compound no.               kg/ha                                                                             max tum nativa                                                                            flexus                                                                             album                                                                              lata exaltata            __________________________________________________________________________    52                         0.5 15  0   0   100  100  100  94                  77                         0.5 --  15  0   80   --   --   80                   ##STR274##                0.5 90  8   10  0    100  --   100                 DE-AS 1,793,226                                                                ##STR275##                0.5  0  33  6   35   72    0   44                  German 1,542,836                                                              65                         1.0 --  5   0   100  95   100  95                  71                         0.5 --  0   0   100  98   100  --                  89                         0.5 --  0   --  100  100  100  100                 58                         1.0 --  5   15  100  100  100  80                  57                         1.0 --  0   10  100  80   100  90                  70                         2.0 --  5   10  100  100  100  95                  85                         1.0 --  5   15  100  98   100  90                  67                         1.0 --  0   0   100  98   100  95                  50                         0.5 --  10  10  100  98   100  80                  80                         1.0 --  10  --  100  100  100  90                  __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________    Selective control of unwanted plants;                                         postemergence treatment in the greenhouse                                                                Test plants and % damage                                                      Ara-     Triti-                                                                           Amaran-        Sesba-                                             chys     cum                                                                              thus-                                                                              Cheno-    nia                     Compound                   hypo-                                                                             Hordeum                                                                            aesti-                                                                           retro-                                                                             podium-                                                                            Lamium                                                                             exal-                   no.                    kg/ha                                                                             gaea                                                                              vulgare                                                                            vum                                                                              flexus                                                                             album                                                                              spp. tata                    __________________________________________________________________________     3                     0.25                                                                              6   5    6  100  100  100  88                       4                     0.25                                                                              20  20   0  100  99   85   80                      28                     1.0 0   0    0  100  90   100  80                       6                     0.25                                                                              15  --   0  100  100  100  --                      41                     1.0 --  0    0  100  98   100  80                      25                     0.5 0   --   0  100  100  100  80                          ##STR276##         0.5 1.0                                                                           4 11                                                                              27 30                                                                              33 40                                                                            65 70                                                                              37 45                                                                              100 100                                                                            82 100                  __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________    Selective control of unwanted plants;                                         postemergence treatment in the greenhouse                                               Test plants and % damage                                            Compound  Gossypium                                                                           Oryza                                                                             Zea                                                                              Cassia                                                                            Cyperus                                                                            Matricaria                                                                          Sesbania                                no.   kg/ha                                                                             hirsutum                                                                            sativa                                                                            mays                                                                             tora                                                                              ferax                                                                              spp.  exaltata                                __________________________________________________________________________    3     0.25                                                                              23    18  16 100 70    82   --                                            0.5 24    24  25 100 86    82    92                                     133   0.5 0     20  10 --  95   100   100                                     60    2.0 8     10  15 --  85   100   100                                     __________________________________________________________________________

                  TABLE 7                                                         ______________________________________                                        Selective control of weeds in sugarbeets and sorghum;                         postemergence treatment in the greenhouse                                               Test plants and % damage                                            Compound        Beta    Sorghum                                                                              Lamium Polygonum                               no.     kg/ha   vulgaris                                                                              bicolor                                                                              spp.   persicaria                              ______________________________________                                        174     2.0     0       10      80    100                                     157     1.0     0       15     100    100                                      60     2.0     0       10     100    100                                     ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                        Herbicidal action on postemergence application in                             the greenhouse                                                                             Test plants and % damage                                         Compound           Euphorbia   Galium                                                                              Mentha                                   no.        kg/ha   geniculat   aparine                                                                             piperita                                 ______________________________________                                        166        3.0     90          --    90                                       128        3.0     90          80    --                                       150        3.0     100         70    80                                        2         3.0     --          --    100                                      148        3.0     100         --    --                                       101        3.0     80          --    --                                       ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        Selective herbicidal action on postemergence application                      in the greenhouse                                                             Com-           Test plants and % damage                                       pound          Triticum Amaranthus                                                                            Chenopo-                                                                             Euphorbia                              no.    kg/ha   aestivum retroflexus                                                                           dium spp.                                                                            geniculata                             ______________________________________                                        148    1.0     15       100     98     86                                     120    0.5     10        95     80     90                                     150    1.0     0        100     100    98                                     128    0.5     0        100     --     98                                     178    0.5     5         95     95     89                                     113    0.5     10        98     98     100                                    172    1.0     0        100     98     --                                     36     0.5     0        100     80     98                                     112    0.5     10       100     98     100                                    158    0.5     5        100     --     80                                     203    0.5     10       100     98     100                                    131    1.0     10       --      98     80                                     142    0.5     0        100     98     90                                     117    1.0     10       100     98     82                                     166    1.0     0        100     --     100                                    1      0.5     10        93     95     100                                    17     1.0     0        100     80     --                                     2      0.5     10       100     98     100                                    15     1.0     0        100     95     --                                     82     1.0     0        --      90     100                                    152    0.5     5        100     100    100                                    ______________________________________                                    

EXAMPLE 6

90 Parts by weight of compound 1 is mixed with 10 parts by weight ofN-methyl-α-pyrrolidone. A mixture is obtained which is suitable forapplication in the form of very fine drops.

EXAMPLE 7

20 Parts by weight of compound 2 is dissolved in a mixture consisting of80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to10 moles of ethylene oxide with 1 mole of oleic acid-N-monoethanolamide,5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid,and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1mole of castor oil. By pouring the solution into 100,000 parts by weightof water and uniformly distributing it therein, an aqueous dispersion isobtained containing 0.02% by weight of the active ingredient.

EXAMPLE 8

20 Parts by weight of compound 3 is dissolved in a mixture consisting of40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol,20 parts by weight of the adduct of 7 moles of ethylene oxide with 1mole of isooctylphenol, and 10 parts by weight of the adduct of 40 molesof ethylene oxide with 1 mole of castor oil. By pouring the solutioninto 100,000 parts by weight of water and finely distributing ittherein, an aqueous dispersion is obtained containing 0.02% by weight ofthe active ingredient.

EXAMPLE 9

20 Parts by weight of compound 1 is dissolved in a mixture consisting of25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oilfraction having a boiling point between 210° and 280° C., and 10 partsby weight of the adduct of 40 moles of ethylene oxide with 1 mole ofcastor oil. By pouring the solution into 100,000 parts by weight ofwater and uniformly distributing it therein, an aqueous dispersion isobtained containing 0.02% by weight of the active ingredient.

EXAMPLE 10

20 Parts by weight of compound 2 is well mixed with 3 parts by weight ofthe sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts byweight of the sodium salt of a lignin-sulfonic acid obtained from asulfite waste liquor, and 60 parts by weight of powdered silica gel, andtriturated in a hammer mill. By uniformly distributing the mixture in20,000 parts by weight of water, a spray liquor is obtained containing0.1% by weight of the active ingredient.

EXAMPLE 11

3 Parts by weight of compound 3 is intimately mixed with 97 parts byweight of particulate kaolin. A dust is obtained containing 3% by weightof the active ingredient.

EXAMPLE 12

30 Parts by weight of compound 4 is intimately mixed with a mixtureconsisting of 92 parts by weight of powdered silica gel and 8 parts byweight of paraffin oil which has been sprayed onto the surface of thissilica gel. A formulation of the active ingredient is obtained havinggood adherence.

EXAMPLE 13

40 Parts by weight of compound 1 is intimately mixed with 10 parts ofthe sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2parts of silica gel and 48 parts of water to give a stable aqueousdispersion. Dilution in 100,000 parts by weight of water gives anaqueous dispersion containing 0.04 wt% of active ingredient.

EXAMPLE 14

20 Parts of compound 2 is intimately mixed with 2 parts of the calciumsalt of dodecylbenzeresulfonic acid, 3 parts of a fatty alcoholpolyglycol ether, 2 parts of the sodium salt of a phenolsulfonicacid-urea-formaldehyde condensate and 68 parts of a paraffinic mineraloil. A stable oily dispersion is obtained.

We claim:
 1. An m-anilide-urethane of the formula ##STR277## where A andB are identical or different and each denotes oxygen or sulfur, and D isoxygen R¹ denotes unsubstituted alkyl; alkyl substituted by halogen,alkoxy, alkoxycarbonyl or cyano; unsubstituted or halogen-substitutedalkenyl; unsubstituted or halogen- or alkoxy-substituted alkynyl; or R¹denotes unsubstituted or alkyl-substituted cycloalkyl or aryl, R² and R³are identical or different and each denotes hydrogen, alkyl, alkoxyalkylor haloalkyl, R⁴ denotes alkylene of 1 to 6 carbon atoms which isunsubstituted or substituted by alkyl, alkoxyalkyl or haloalkyl, Xdenotes hydrogen, alkyl, haloalkyl, alkoxy, halogen, nitro or amino, Ydenotes hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, aralkyl,halogen, or alkenyl chain fused with the benzene ring to give abromo-substituted or unsubstituted naphthyl ring, Y further denotesalkoxy, haloalkoxy, alkylthio, nitro, aryl, thiocyanato, cyano,##STR278## R⁵ and R⁶ being identical or different and each denotinghydrogen or having the meanings given for R¹, m denotes one of theintegers 1, 2, 3 and 4, and n denotes one of the integers 1, 2, 3, 4 and5.
 2. A compound of claim 1 having the formula ##STR279##
 3. Anm-anilide-urethane selected from the group consisting of ##STR280##